Petroleum substitutes from the essential oils of eupatorium species

ABSTRACT

The essential oils of  Eupatorium capillifolium  (Dogfennel) and  Eupatorium compositifolium  (Yankeeweed) may be isolated in unexpectedly high yield by steam distillation of the whole or leafy parts of the plants. Such oils may be used as motor fuels in gasoline and diesel engines in unrefined and refined form.  Eupatorium  oil is amenable to separation into lower boiling and higher boiling fractions better suited to gasoline and diesel fuel use, respectively. It is also amenable to refining by hydrogenation, dehydrogenation, reforming, cracking and alkylation of the whole oil or isolated components thereof.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a method for the economical production of biofuels from the plant matter of invasive weed-type plants. Specifically, gasoline substitute and diesel fuel substitute may be prepared by the steam distillation of members of the plant genus Eupatorium

2. Description of the Prior Art

United States energy planning currently includes programs for the production of ethanol from corn, switchgrass and biomass as a way to supplement gasoline stocks. The production of fatty acid methyl esters or biodiesel fuels from soybean and sunflower oil is envisioned as a means to supplement diesel fuel stocks. However, ethanol production uses up to 57% more fossil fuel energy respectively than it replaces. See Pimentel, D.; Patzek, T. W., Ethanol Production using Corn, Switchgrass, and Wood; Biodiesel Production Using Soybean and Sunflower, Natural Resources Research (2005) Vol. 14, pp 65-76. Biodiesel fuel production uses from about 27% to 118% more fossil fuel energy than produced just to produce the raw vegetable oil. Further, most of these raw materials are foodstocks that are arguably better utilized to feed the populace. The agricultural regions of the U.S. south are subject to invasion by a host of weed-like plants. Among these are plants of the genus Eupatorium. Eupatorium compositifolium (Yankeeweed or Banker's Weed) and Eupatorium capillifolium are tall, invasive plants that give off a pepper-like aroma when disturbed. Over a century ago, the essential oils of these plants were isolated and crudely described [Perry] as mostly containing phellandrene. More recently publications have described the alkaloids. See Dominguez, X. A.; Gomez, M. E.; Gomez, P., A.; Villarreal, A. N.; Rombold, C., Physical Data on the Essential Oils of Five Compositae Plants, Planta Medica October 1970 Vol. 19 pp. 52-54;

-   essential oils[Hegnauer, Dominguez}, flavanoids. See Wagner, H.;     Iyengar;, M. A., Horhammer, L; Herz, W., Flavonol-3-glycosides in     eight Eupatorium Species, Phytochemistry (1972) Vol. 11 pp     1504-1505; -   Herz, W.; Gibaja, S.; Bhat, S. V.; Srinivasan, A., Dihydroflavanols     and other Flavonoids of Eupatorium Species, Phytochemistry (1972)     Vol. 11 pp 2859-2863. -   and sesquiterpenes [Rao, Sadhu] found in Eupatorium capillifolium.     The description of the essential oils is, however, sparse, listing     the main component as 65% limonene “plus three other components”.     The essential oils of Eupatorium species have found trivial utility     as insect repellant and remedy for bites. U.S. Pat. Nos. 6,509,480     and 6,326,396 claim glucose and lipid lowering properties of some of     the components of E. capillifolium.

The prior art discloses that there is a great deal of technology developed for destroying Eupatorium species. U.S. Pat. No. 4,401,602 describes 4-trifluoromethylphenoxy benzaldoximes as herbicides for killing E. capillifolium. U.S. Pat. Nos. 4,169,719 and 4,127,405 describe herbicidal sulfonamides with the same capability. U.S. Pat. Nos. 4,028,090 and 3,959,303 describe 5-cyanoalkyl-1,3,4-thiadiazol-2-ylureas as alternative herbicides for killing E. capillifolium.

SUMMARY OF THE INVENTION

The invention describes a convenient and economical method for producing biofuels directly from plants of genus Eupatorium without concomitant fermentation or transesterification. This may be effected according to the steps of:

-   -   (1) Growing and harvesting the weed species E. capillifolium         or E. compositifolium as intentional field crops.     -   (2) Steam distilling the whole plants or plant parts to produce         crude Eupatorium oils.     -   (3) Optionally, further separating, purifying or refining.     -   (4) Using the Eupatorium oils as a petroleum replacement (i.e.         motor fuel, lubricant).

According to the present invention, the essential oils of Eupatorium species may be used as motor fuels and produced for such in an economical and energy positive manner.

DETAILED DESCRIPTION OF THE INVENTION

Many field weeds exude an aromatic fragrance, particularly when disturbed. It is reasonable to expect that the chemical compounds that make up these fragrances may be isolated by various means. In fact, there is a long history of plant species having been extracted to yield their volatile or ‘essential oils’. Lemon oil, wintergreen oil and sandalwood oil are examples. Generally, these essential oils find utility as fragrances and flavorings, though some are poisonous in nature. The most common isolation techniques are solvent extraction and steam distillation.

In one embodiment of this invention, the volatile oils from Dogfennel and/or Yankeeweed art combustable and usable as a petroleum substitute, more specifically as a motor fuel in an internal combustion engine. These oils, detectable as a fragrance, have significant volatility to be a gasoline and b) are contained within the plant in an appreciable quantity. Upon isolation, it was found that despite their apparent volatility, the oils have a boiling point ranging from about 150° C. to about 270° C. In petroleum science, this range is recognized more to be the ranges of heavy naphtha and kerosene than that of a straight run gasoline fraction. See Chenier, P. J., Survey of Industrial Chemistry, 2^(nd) Ed. (1992) pp 113-136. While heavy naphtha is useful for the production of gasoline, kerosene it is more useful as diesel, jet and heating fuel. In another embodiment of this invention, Dogfennel and/or Yankeeweed oil, or fractions thereof, are used straight or refined as either a gasoline substitute or a diesel, jet, or fuel oil substitute.

In a further embodiment of this invention, straight Dogfennel and/or Yankeeweed oil may be used as fuel in a gasoline powered internal combustion engine (Y-18). As such, unrefined Yankeeweed oil is used as fuel for a 2.8 cubic inch (46 cc) chain saw engine. The engine was run initially on gasoline and then transitioned, without stopping, to Yankeeweed oil as fuel. No engine adjustments were made. This type of engine was particularly suited to this type of experiment as it has no ‘bowl’ reservoir typical of carbureted engines. Such a bowl would allow for mixing between the initial gasoline fuel and the following Yankeeweed oil fuel. A modern fuel injected engine would also not have such a mixing problem.

As further proof of this concept, unrefined Yankeeweed oil is used as fuel for a 280 cubic inch (4.6 L) 8 cylinder automobile engine. The engine was run initially on gasoline and then transitioned without stopping to Yankeeweed oil as fuel. No engine adjustments were made.

In another embodiment of this invention, straight Dogfennel and/or Yankeeweed oil is used as fuel in a diesel powered internal combustion engine. As such, unrefined Yankeeweed oil is used as fuel for a XXX cubic inch (4.5 L) tractor engine. The engine was run initially on diesel and then transitioned without stopping to Yankeeweed oil as fuel. No engine adjustments were made.

The essential oil of Dogfennel has been reported to be isolated by steam distillation in 0.50% recovery. See Dominguez et al, ibid. There have been no reports of the yield from the closely related Yankeeweed. In an initial kilo scale experiment (Y-8), an oil recovery of 0.54% is obtained, indicating a generality in the oil recovery for the two species.

In an additional embodiment of this invention, it has been discovered that by separating the distillate oils from the distillate water and returning the distillate water to the boiling vessel, or using an apparatus that continually returns separated distillate water to the boiling vessel, the recovery of oils increases dramatically to 0.70-0.80%. This is due to the discovery that there is an appreciable solubility of the oils in water. By recycling oil-saturated water to the boiling vessel, this quantity of dissolved oil is not lost as it would be if the distillate water was discarded.

High yields of essential oils from fragrant plant species is not an obvious expectation. Perilla mint (Perilla frutescens) is an extremely fragrant field plant that grows in overlapping ranges with the Eupatorium species. However, isolation of its essential oil by the identical steam distillation method that had such high yields with Yankeeweed, gave very low yields of Perilla Mint oil (Y-15).

The oil from Eupatorium species, referred to herein as Eupatorium oil, may be isolated by any method known to the art for the isolation of essential oils from plants. However, some methods, such as solvent extraction are not selective and also isolate undesirable compounds such as chlorophyll and tannin along with the essential oils. Also, much of the solvent may be lost with the spent plant residue. Supercritical CO₂ may have some utility with this regard. Pressing is an option, but much of the oil remains with the residual plant matter.

In the case of Eupatorium oil, the preferred method for isolation is steam distillation. This may be performed in batch or continuously.

In a batch process, a boiler is charged with plant matter and water and distillation of the water is performed. The distillation may be what is considered ‘simple’, that is distillate is removed through a condenser until oil ceases to express or until the boiler water has been removed to practical limits. A liquid/liquid separation of the condensed distillate into oil fraction and water fraction necessarily follows. The distillation may also be of the continuous separation type, i.e., Dean-Stark distillation. In this procedure, distillate is condensed and collected in a small accumulator. Liquid/liquid separation occurs and the distillate water fraction is returned to the boiler more or less continuously. The distillate oil fraction is removed to a receiver more or less continuously. Either of the batch methods for the isolation of Eupatorium oil has the disadvantage of requiring a large boiler and a time consuming charge/fill/heat/cool/drain/empty cycle. In this case, dual equipment allows the staggering of this cycle with increased efficiency. Heating and cooling of the boiler water can be minimized by transfer of the same water charge between the boilers.

In a continuous process, a boiler is charged with water and then plant matter is introduced continuously, typically at one end of the boiler. The spent plant matter is removed from the boiler continuously, typically at the other end of the boiler. The plant matter is moved through the boiler by gravity, water-flow (jets) or mechanical means from the entrance to the exit. Mechanical means may be augers or continuous belts or chains. The plant matter may be free or contained in baskets or carts. The rate of movement is such as to allow a residence time of the plant matter within the boiler sufficient to allow the distillation of a satisfactory quantity of the plant oils. Just like the batch process, it is advantageous to recycle distillate water back to the boiler (rather than continuously feed fresh water). It is preferred that the boiler be equipped with a Dean-Stark style accumulator to separate the product oils and continuously return distillate water to the boiler. This has the added benefit of conserving heat within the distillate water for efficient re-boiling. It is preferable that the entrance and exit of the boiler are constructed such that distillate vapors may not escape during charging and withdrawal of the plant matter. A rotating vapor lock, similar to a revolving door is one applicable construction. Another means for retaining distillate vapors within the boiler is to employ a cooled, raised hopper that serves as entrance and/or exit to the boiler, i.e., a raised hopper charges and /or withdraws plant matter through the bore of a large upright condenser. The chamber need not be tubular as is typically the case with a condenser, but may be of dimensions convenient for the passing of plant matter through it, particularly the side-ways feeding of whole plants. Some water will be lost as the spent plant material remains wetted. This loss may be continuously or intermittently made-up with fresh water.

In any of these processes, the injection of high temperature steam may be employed as a heat source and a means of performing the distillation.

In any of these processes, salt water or brine may be used as the boiler water. With the proper materials of construction, acidic water may be used as the boiler water. It is known in the biological arts that solutions of high salt content or solutions of high acidity facilitate the rupturing of cell walls. This can be advantageous in accelerating the release of essential oils from plant matter.

The plant matter from Eupatorium species may be steam distilled whole or in parts. Whole plant has the advantage of ease of transport within boilers set-up for continuous mechanical transport. Chopped plant matter has the advantage of ease of transport within boilers set-up for continuous gravity or water-flow transport. Chopping or crimping has no significant effect on the yield of oil. The essential oils are contained primarily in the leafy green portion of the plant. As such, whole plant may have non-leafy stem portions removed without loss of yield. Such stem removal may be employed as a means to increase throughput in the distillation process.

The Eupatorium oil may be refined as necessary by any of the processes known in the art for refining petroleum. In general, the oil may be subjected to alkylation, cracking, hydrogenation, reforming in order to modify its properties.

The Eupatorium oil is useful as a solvent, degreaser and paint thinner. It may also be used as a wood finishing agent.

In another embodiment of this invention, Eupatorium species are cultivated and harvested as intentional crops. Dogfennel and Yankeeweed are both considered to be unwanted and invasive field weeds (though some decorative garden use has been noted). As set forth above, a great deal of effort has been made in the herbicide industry towards their destruction. Both Eupatorium species grow wild and may be observed on roadsides and in unkempt fields. They are very hardy, drought resistant plants that can grow in low quality soil. As annuals, the original plant survives winter and regrows from its rootstock. When cut-off, both species grow new shoot from the rootstock. Dogfennel and Yankeeweed reproduce by seed and are extremely prolific. However, in order to be economically viable as a source of petroleum replacement, Dogfennel and Yankeeweed must be intentionally cultivated.

Both Eupatorium species are perennial plants that reproduce by wind-borne seed. As such, Dogfennel and Yankeeweed are self planting, once established (Corn and soybean are annual and must be planted for each crop at considerable expense). In an additional embodiment of this invention, Eupatorium species may be cultivated by the dispersal of seed over a suitable plot of agricultural land. This technique establishes a field of Eupatorium within one growing season. Another embodiment of this invention is to plant Dogfennel and/or Yankeeweed seed in very widely spaced rows within a suitable plot of agricultural land. The resulting rows of plants are allowed to fully mature and to naturally disperse their seed upon the unplanted space between the original intentionally planted rows. This method has the advantage of requiring less initial seed and seeding, but requires two growing seasons to execute.

Dogfennel and Yankeeweed may be harvested by means commonly available to current farmers. The plants may be harvested by combine as is wheat. The combine would cut and gather the plant material and load it into a truck or wagon for transport. Winnowing is, however, not necessary. The plants may be harvested by cutter as is hay. A cutter would cut the plants and they may then be raked and gathered as desired. The plants may be baled, if desired, by any of the equipment currently in use for hay, the larger type balers being more efficient.

In another embodiment of this invention, the plants may be harvested throughout the growing season. Whereas corn for gasohol and soybean for biodiesel fuels must be harvested as the mature fruits, Dogfennel and Yankeeweed contain recoverable oils throughout the lifetime of the plant. Plants may be harvested as soon as they reach an economically practical size. The yield of oils is higher when the plants are in bud, flower or seed, however it is economically practical to harvest some immature plants so as to have continuous operation of facilities and continuous production of oil through as much of the calendar year as possible. With this regard, baled or otherwise stored plants are an useful in the present invention. An unexpected advantage to the harvesting of immature plants is the ability of both Dogfennel and Yankeeweed to re-sprout after cutting. In a further embodiment of this invention, immature plants are cut and harvested early in the growing season. Cut plants re-grow and most often re-grow branched, with increased plant mass. Such re-growth may be then harvested later in the growing season for a second crop.

In another embodiment of this invention, established agricultural plots of Dogfennel and Yankeeweed are maintained and reproduced by several means, including harvesting whole plants, then relying on re-growth from the root-stock to maintain the plant population. Alternatively, certain amount of plants may intentionally remain un-harvested in each plot. The un-harvested plants are allowed to mature and re-plant the surrounding areas via their windborne seeds. A convenient means for accomplishing this is to leave a certain proportion of rows uncut (i.e. 1 in 100). A further alternative is to cut the plants high on the stem during late season harvesting. If such a cut is high enough to leave at least one green leafy branch on the stump, the plant will flower and seed from that branch. This procedure has the added advantage of not harvesting the non oil-bearing stem and obviating a later stem cutting prior to the distillation process.

In a further embodiment of this invention, the growth of competitive plants is suppressed. As mentioned above, many herbicides have been formulated to kill Dogfennel and Yankeeweed, however, many do not. In this embodiment of this invention, plots of Dogfennel and/or Yankeeweed are enhanced by the suppression of other plant species. Any herbicide that kills or suppresses agricultural weed, but does not suppress Dogfennel and/or Yankeeweed may be utilized. Eupatorium oil, distillate water and boiler water may be used in this role to some advantage. It is not necessary, but is advantageous to suppress other plants from a Dogfennel and/or Yankeeweed plot. The advantage is to maintain as high a recovery of oil per hectare as possible. For example, a population of grasses within the plot will detract from the overall recovery. Other plants may produce some quantity of essential oils, but it expected that their contribution will still lower overall recovery. However, any oils generated by these plants should have no detrimental effect to the quality of the Eupatorium oil as a fuel as they will retain the same approximate properties of the distillate oil.

In an additional embodiment of this invention, the residual plant material, referred to in the sugar industry as bagasse are used as solid fuel. Such solid fuel is used to fuel the distillation boiler, or any other boiler. Preliminary drying may be necessary, but this is readily accomplished with the residual heat of the distillation boiler. The residual plant matter may be used to make pulp for paper production. The stem material in particular is high in cellulose and has been cleaned of many undesirable components by boiling. The residual plant material may be used as animal feed. One biological function of the essential oils of any plant is to make the plant less palatable to herbivores. As the process of this invention effectively strips the plant matter of these protective oils, the plant material is more palatable and may be used as feed or incorporated into feed mixtures.

The residual boiler water may be used as fertilizer for Eupatorium or other crops. This water contains dissolved minerals and washed-off soil that is advantageously returned to the field. Particularly in continuous processes such as described above, such minerals and soil becomes concentrated over time. The residual boiler water may also be used as feed liquor to an ethanol fermentation process. This water contains dissolved sugars and polysaccharides that may be fermented into ethanol. Particularly in continuous processes, such sugars and polysaccharides become concentrated over time.

Off-gases from the process may be collected to some advantage. By low temperature condensation or compression, the non-condensable components of the distillate may be recovered. Compounds such as hydrogen sulfide, alkyl sulfides, alkyl disulfides and dialkyl disulfides may be retained for their economic value.

EXAMPLE 1

Isolation of Petroleum Substitute from Eupatorium by Continuous Steam Distillation.

Into a 1000 mL round bottomed flask fitted with a Dean-Stark collector and water cooled condenser was charged 200 grams of chopped Yankeeweed leaf and 600 mL of water. The flask was heated to reflux and the distillate collected in the Dean-Stark apparatus. Distillate water was returned to the flask in 100 mL portions and the separated oils drawn off to a tared bottle. After 500 mL of distillate water had passed through the system, the distillation was stopped and the round bottom flask emptied. The round bottom flask was then re-charged with 200 grams fresh Yankeeweed leaf and 600mL of fresh water. The above distillation procedure was repeated for a total of 5 consecutive runs. The product oils were combined to yield 10.0 grams of light yellow oil. Recovery of oils was 1.0% by weight vs. Yankeeweed leaf.

EXAMPLE 2 (COMPARATIVE)

Isolation of Petroleum Substitute from Eupatorium by Liquid Extraction

Into an electric blender was placed 200 grams of chopped Yankeeweed leaf and 500 mL of water. The mixture was blended to a puree and transferred to a separatory funnel. The puree was extracted 3× with 200 mL diethyl ether. The ether was evaporated to yielding a dark green gum.

EXAMPLE 3

Isolation of Petroleum Substitute from Eupatorium by Batch-wise Steam Distillation.

A 55 gallon direct fired steel boiler, fitted with a claisen head and 10 ft×¾ inch steel condenser was charged to fullness with 100 lbs. of whole Yankeeweed. The boiler was then charged with and 30 gallons of fresh water. The boiler was heated to 101-102° C. and the distillate collected in 5 gallon portions into separate receivers isolated within a steel drum and chilled with a ½ inch×10 foot refrigerated cooling coil. After 20 gallons of distillate had been collected, the distillation was stopped. Each portion of distillate was allowed to settle 1 hour and separated with a separatory funnel. Recovery of oils was 0.54 lbs (0.54% by weight vs. whole Yankeeweed).

EXAMPLE 4

Isolation of Petroleum Substitute from Eupatorium by Batch-Wise Steam Distillation with Recycled of Distillate Water.

A 55 gallon direct fired steel boiler, fitted with a claisen head and 20 ft×¾ inch steel condenser was charged to fullness with 62 to 86 lbs. of whole Yankeeweed. The boiler was then charged with 30 gallons of recovered distillate and boiler water from the immediately previous distillation. The boiler was heated to 101-102° C. and the distillate collected in 5 gallon portions into separate receivers without the benefit of any further cooling. After 20-25 gallons of distillate had been collected, the distillation was stopped. Each portion of distillate was allowed to settle 1 hour and separated with a separatory funnel. Recovery of oils ranged from was 0.70 to 1.27% by weight vs. whole Yankeeweed.

TABLE 1 Recovery by Weight of Yankeeweed Oil by Portion of Distillate Exp 8 10 13 16 19 Date 8/27 8/30 9/4 9/14 9/25* Pounds 100 79 86 75 62 Portion 1 0.27 0.41 0.41 0.40 0.69 Portion 2 0.16 0.13 0.21 0.28 0.23 Portion 3 0.09 0.12 0.09 0.10 0.16 Portion 4 0.01 0.05 0.04 0.07 0.10 Portion 5 — — 0.02 — 0.08 Total 0.54 0.71 0.76 0.70 1.27 *Plants in bud

EXAMPLE 5

Attempted Isolation of Petroleum Substitute from Perilla Frutescens by Batch-wise Steam Distillation. (Comparative)

A 55 gallon direct fired steel boiler, fitted with a claisen head and 20 ft×¾ inch steel condenser was charged to fullness with 70 lbs. of whole Perilla Mint. The boiler was then charged with and 35 gallons of fresh water. The boiler was heated to 101-102° C. and the distillate collected in 5 gallon portions into separate receivers. After 30 gallons of distillate had been collected, the distillation was stopped. Each portion of distillate was allowed to settle 1 hour and separated with a separatory funnel. There was no recovery of oils. The distillate had an oily sheen and the scent of mint, indicating the likelihood of solubilized oils.

EXAMPLE 6 (COMPARATIVE)

Isolation of Petroleum Substitute from Perilla Frutescens by Batch-Wise Steam Distillation with Recycled of Distillate Water.

A 55 gallon direct fired steel boiler, fitted with a claisen head and 20 ft×¾ inch steel condenser was charged to fullness with 70 lbs. of whole Perilla Mint. The boiler was then charged with 30 gallons of recovered distillate and boiler water from the immediately previous distillation. The boiler was heated to 101-102° C. and the distillate collected in 5 gallon portions into separate receivers without the benefit of any further cooling. After 20 gallons of distillate had been collected, the distillation was stopped. Each portion of distillate was allowed to settle 1 hour and separated with a separatory funnel. Recovery of oils was 0.015 lbs (0.02% by weight vs. whole Perilla Mint).

EXAMPLE 7 Purification of Eupatorium Oil by Atmospheric Pressure Distillation (Y-7)

A 250 mL round bottom flask was fitted with a one piece glass simple distillation apparatus and charged with 119 grams of unrefined Yankeeweed oil. The condenser portion of the distillation apparatus was chilled with −10° C. coolant fluid. The flask was heated to boiling and the distillate collected into an iced receiver. A forerun consisting of mostly water was collected at an overhead temperature of 96 to 100° C. The remainder of the distillate was collected at an overhead temperature that ranged from 130 to 260° C. Higher temperatures were not possible in the apparatus used. The recovery of purified oil was 103 grams (87%).

EXAMPLE 8 Purification of Eupatorium Oil by Vacuum Distillation (Y-9)

A 250 mL round bottom flask was fitted with a short vigareaux distillation column, topped with a one piece glass simple distillation apparatus and charged with 172 grams of unrefined Yankeeweed oil. The condenser portion of the distillation apparatus was chilled with −20° C. coolant fluid. A vacuum of 100 microns was established and the flask was heated to boiling. A forerun consisting of mostly water was allowed to pass through the receiver uncollected. The remainder of the distillate was collected into an iced receiver at an overhead temperature that ranged from 48 to 112° C. The recovery of purified oil was 167 grams (97%).

EXAMPLE 9 Purification of Eupatorium Oil by Continuous Steam Distillation.

Into a 1000 mL round bottomed flask fitted with a Dean-Stark collector and water-cooled condenser was charged 225 grams of unrefined Yankeeweed oil and 550 mL of water. The flask was heated to reflux and the distillate collected in the Dean-Stark apparatus. Distillate water was returned to the flask in 100 mL portions and the separated oils drawn off to a tared bottle. After 3000 mL of distillate water had passed through the system, the distillation appeared complete and was stopped. The recovery of purified oil was 223 grams (99%).

EXAMPLE 10 Refining of Eupatorium Oil by Hydrogenation

A 10 mL glass pressure bottle was charged with 0.15 grams of distilled Yankeeweed Oil, 0.02 grams of 10% palladium on carbon, and 1.0 mL of hexanes. Gas chromatographic analysis indicated that the unreacted oil consisted of four general regions of components, designated for convenience as Regions A-D. The bottle was sealed and charged with 50 psi H₂ gas. After 24 hour of reaction at room temperature, gas chromatographic analysis indicated that the 9 products of “Region A” interpreted to be terpenes had coalesced into only 4 products. Other regions of the chromatograph exhibited simplification. The sample was resubmitted to 100 psi H₂ gas for 48 hours. Changes in the composition of “Region B” were observed, indicative of hydrogenation.

EXAMPLE 11 Refining of Eupatorium Oil be Dehydrogenation (and Aromatization). EXAMPLE 11a Demonstration of Eupatorium Oil as a Motor Fuel (Mogas)

A 2.8 cubic inch (46cc) gasoline powered chain saw engine was modified slightly to allow introduction of fuel from a 60 mL measured buret rather than the stock fuel tank. The buret was filled with 20 mL gasoline fuel and the engine was started. The engine was run at full throttle until the buret read zero. A charge of 6 mL of 2:1 gasoline/Yankeeweed oil was poured into the buret while holding the throttle at full power. The engine continued to function using the 6 mL mixture as fuel until it was all consumed. The buret was re-filled with 5 mL gasoline fuel and the engine was re-started. The engine was run at full throttle until the buret read zero. A charge of 8 mL of 1:1 gasoline/Yankeeweed oil was poured into the buret while holding the throttle at full power. The engine continued to function using the 8 mL mixture as fuel until it was all consumed. The buret was re-filled with 5 mL gasoline fuel and the engine was re-started. The engine was run at full throttle until the buret read zero. A charge of 20 mL of 0:1 gasoline/Yankeeweed oil (i.e. pure oil) was poured into the buret while holding the throttle at full power. The engine continued to function, consuming 10 mL of Yankeeweed oil as fuel at which point the engine was allowed to idle. After 30 seconds of successful idling, the engine was returned to full throttle, returning to full power and consuming another 8 mL of Yankeeweed oil as fuel. The engine was returned to idle and ran until the remaining 2 mL of Yankeeweed oil fuel was consumed. 

1. Petroleum substitutes derived from plant matter of the genus Eupatorium.
 2. The Petroleum substitutes derived from plant matter according to claim 1 comprising the species Eupatorium compositifolium (Yankeeweed or Banker's Weed), the species Eupatorium capillifolium (Dogfennel) or Eupatorium foeniculaceum.
 3. The Petroleum substitutes derived from plant matter according to claim 2 that is a gasoline substitute, a diesel fuel substitute, a jet fuel substitute, a lamp oil substitute, a stove fuel substitute or a fuel oil substitute.
 4. A process for the isolation of the oils of the genus Eupatorium comprising the steam distillation of Eupatorium plant matter.
 5. The process according to claim 4 wherein said steam distillation of Eupatorium plant matter comprises the continuous feeding of the plant matter.
 6. The process according to claim 5 wherein said steam distillation of Eupatorium plant matter further comprises the continuous removal of spent plant matter or spent extracts of the plant matter.
 7. The process according to claim 5 wherein said steam distillation of Eupatorium plant matter further comprises the continuous generation of distillate water and dissolved components.
 8. The process according to claim 5 wherein said steam distillation of Eupatorium plant matter further comprises the continuous collection of distillate water and dissolved components.
 9. The process according to claim 5 wherein said steam distillation of Eupatorium plant matter further comprises the continuous recycle of distillate water and dissolved components.
 10. The process according to claim 5 wherein said steam distillation of Eupatorium plant matter further comprises he continuous collection of product oils.
 11. The process according to claim 5 wherein said steam distillation of Eupatorium plant matter further comprises the continuous removal and isolation of product oils.
 12. A process wherein the spent plant matter from the steam distillation of the species Eupatorium is used as boiler fuel, digestable or fermentable biomass for ethanol production or as pulp for papermaking.
 13. A process constituting the fermentation of boiler water recovered from the steam distillation of the species Eupatorium and the isolation of ethanol from said fermentation.
 14. The process according to claim 13 wherein said ethanol is used as a motor fuel. 